Visual Chiral Recognition through Enantioselective Metallogel Collapsing: Synthesis, Characterization, and Application of Platinum–Steroid Low-Molecular-Mass Gelators†
Corresponding Author
Dr. Tao Tu
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorWeiwei Fang
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Search for more papers by this authorXiaoling Bao
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Search for more papers by this authorXinbao Li
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Search for more papers by this authorProf. Karl Heinz Dötz
Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn (Germany)
Search for more papers by this authorCorresponding Author
Dr. Tao Tu
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412Search for more papers by this authorWeiwei Fang
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Search for more papers by this authorXiaoling Bao
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Search for more papers by this authorXinbao Li
Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai (China), Fax: (+86) 21-65102412
Search for more papers by this authorProf. Karl Heinz Dötz
Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn (Germany)
Search for more papers by this authorFinancial support from the National Natural Science Foundation of China (No. 20902011), the Shanghai Municipal Science and Technology Commission (Qimingxing Program No. 10A1400500), the Shanghai Leading Academic Discipline Project (B108), and Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials (2010MCIMKF04), Department of Chemistry, Fudan University is gratefully acknowledged. We thank Prof. Tao Yi and Prof. Qi-Lin Zhou for technical support.
Graphical Abstract
Sehen um zu glauben: Die optische chirale Erkennung von (R)- und (S)-Binap gelang mithilfe des enantioselektiven Kollabierens von Metallogelen, die mit neuartigen Gelatoren aus Platin und Pinzettenliganden mit aromatischem, Linker- und Steroidteil hergestellt wurden. Van-der-Waals-Wechselwirkungen, π-Stapelung und Metall-Metall-Bindung führen zur Aggregation und chiralen Erkennung.
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References
- 1
- 1a Chiral Recognition in the Gas Phase (Ed.: ), Woodhead, Cambridge, UK, 2010;
- 1b Chirality in Drug Research (Eds.: ), Wiley-VCH, Weinheim, 2006;
- 1c Chirality in Natural and Applied Science (Eds.: ), Blackwell, Oxford, UK, 2002.
- 2
- 2aSelected recent reviews of chiral recognition: G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1;
- 2bL. Pu, Chem. Rev. 2004, 104, 1687;
- 2cM. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479;
- 2dF. Vögtle, P. Knops, Angew. Chem. 1991, 103, 972;
10.1002/ange.19911030810 Google ScholarAngew. Chem. Int. Ed. Engl. 1991, 30, 958.
- 3
- 3aH.-L. Liu, Q. Peng, Y.-D. Wu, D. Chen, X.-L. Hou, M. Sabat, L. Pu, Angew. Chem. 2010, 122, 612; Angew. Chem. Int. Ed. 2010, 49, 602;
- 3bL. Chi, J. Zhao, T. D. James, J. Org. Chem. 2008, 73, 4684;
- 3cZ.-B. Li, J. Lin, M. Sabat, M. Hyacinth, L. Pu, J. Org. Chem. 2007, 72, 4905;
- 3dJ. Heo, C. A. Mirkin, Angew. Chem. 2006, 118, 955;
10.1002/ange.200503343 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 941.
- 4
- 4aS. J. Wezenberg, E. C. Escudero-Adán, J. Benet-Buchholz, A. W. Kleij, Org. Lett. 2008, 10, 3311;
- 4bB. García-Acosta, R. Martínez-Máñez, J. V. Ros-Lis, F. Sancenón, J. Soto, Tetrahedron Lett. 2008, 49, 1997;
- 4cW. Kaminsky, E. Haussühl, L. D. Bastin, J. A. Subramony, B. Kahr, J. Cryst. Growth 2002, 234, 523;
- 4dK. Tsubaki, M. Nuruzzaman, T. Kusumoto, N. Hayashi, B.-G. Wang, K. Fuji, Org. Lett. 2001, 3, 4071;
- 4eY. Kubo, S. Maeda, S. Tokita, M. Kubo, Nature 1996, 382, 522;
- 4fT. Nishi, A. Ikeda, T. Matsuda, S. Shinkai, J. Chem. Soc. Chem. Commun. 1991, 339;
- 4gT. Kaneda, K. Hirose, S. Misumi, J. Am. Chem. Soc. 1989, 111, 742.
- 5H.-L. Liu, X.-L. Hou, L. Pu, Angew. Chem. 2009, 121, 388; Angew. Chem. Int. Ed. 2009, 48, 382.
- 6Selected recent reviews:
- 6a Molecular Gels: Materials with Self-Assembled Fibrillar Networks (Eds.: ), Springer, Dordrecht, 2006;
- 6bM. George, R. G. Weiss, Acc. Chem. Res. 2006, 39, 489;
- 6c“Low Molecular Mass Gelator”, Top. Curr. Chem. 2005, 256, 1;
- 6dN. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821;
- 6eF. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491;
- 6fL. A. Estroff, A. D. Hamilton, Chem. Rev. 2004, 104, 1201;
- 6gJ. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351;
Angew. Chem. Int. Ed. 2000, 39, 2263.
10.1002/1521-3773(20000703)39:13<2263::AID-ANIE2263>3.0.CO;2-V CAS PubMed Web of Science® Google Scholar
- 7
- 7aX. Yu, Q. Liu, J. Wu, M. Zhang, X. Cao, S. Zhang, Q. Wang, L. Chen, T. Yi, Chem. Eur. J. 2010, 16, 9099;
- 7bJ. Wu, T. Yi, T. Shu, M. Yu, Z. Zhou, M. Xu, Y. Zhou, H. Zhang, J. Han, F. Li, C. Huang, Angew. Chem. 2008, 120, 1079; Angew. Chem. Int. Ed. 2008, 47, 1063.
- 8
- 8aX. Chen, Z. Huang, S.-Y. Chen, K. Li, X.-Q. Yu, L. Pu, J. Am. Chem. Soc. 2010, 132, 7297;
- 8bM. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. 2001, 113, 633;
10.1002/1521-3757(20010202)113:3<633::AID-ANGE633>3.0.CO;2-R Google ScholarAngew. Chem. Int. Ed. 2001, 40, 613.10.1002/1521-3773(20010202)40:3<613::AID-ANIE613>3.0.CO;2-K CAS PubMed Web of Science® Google Scholar
- 9F. Fages, Angew. Chem. 2006, 118, 1710;
10.1002/ange.200503704 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 1680.
- 10J. Liu, P. He, J. Yan, X. Fang, J. Peng, K. Liu, Y. Fang, Adv. Mater. 2008, 20, 2508.
- 11
- 11aA. Gansäuer, I. Winkler, T. Klawonn, R. J. M. Nolte, M. C. Feiters, H. G. Börner, J. Hentschel, K. H. Dötz, Organometallics 2009, 28, 1377;
- 11bT. Klawonn, A. Gansäuer, I. Winkler, T. Lauterbach, D. Franke, R. J. M. Nolte, M. C. Feiters, H. Börner, J. Hentschel, K. H. Dötz, Chem. Commun. 2007, 1894.
- 12
- 12aT. Tu, X. Bao, W. Assenmacher, H. Peterlik, J. Daniels, K. H. Dötz, Chem. Eur. J. 2009, 15, 1853;
- 12bT. Tu, W. Assenmacher, H. Peterlik, G. Schnakenburg, K. H. Dötz, Angew. Chem. 2008, 120, 7236; Angew. Chem. Int. Ed. 2008, 47, 7127;
- 12cT. Tu, W. Assenmacher, H. Peterlik, R. Weisbarth, M. Nieger, K. H. Dötz, Angew. Chem. 2007, 119, 6486; Angew. Chem. Int. Ed. 2007, 46, 6368.
- 13
- 13aT. Tu, X. Feng, Z. Wang, X. Liu, Dalton Trans. 2010, 39, 10598;
- 13bT. Tu, H. Mao, C. Herbert, M. Xu, K. H. Dötz, Chem. Commun. 2010, 46, 7796;
- 13cT. Tu, J. Malineni, X. Bao, K. H. Dötz, Adv. Synth. Catal. 2009, 351, 1029;
- 13dT. Tu, J. Malineni, K. H. Dötz, Adv. Synth. Catal. 2008, 350, 1791.
- 14A. Takahashi, M. Sakai, T. Kato, Polym. J. 1980, 12, 335.
- 15
- 15aP. Terech, F. Volino, R. Ramasseul, J. Phys. 1985, 46, 895;
- 15b Small-Angle X-ray Scattering (Eds.: ), Academic Press, London, 1982.
- 16Selected examples:
- 16aJ. J. Yan, A. L.-F. Chow, C.-H. Leung, R. W.-Y. Sun, D.-L. Ma, C.-M. Che, Chem. Commun. 2010, 46, 3893;
- 16bY. Chen, K. Li, W. Lu, S. S.-Y. Chui, C.-W. Ma, C.-M. Che, Angew. Chem. 2009, 121, 10093; Angew. Chem. Int. Ed. 2009, 48, 9909;
- 16cW. Lu, S. S.-Y. Chui, K.-M. Ng, C.-M. Che, Angew. Chem. 2008, 120, 4644; Angew. Chem. Int. Ed. 2008, 47, 4568;
- 16dW. Lu, N. Zhu, C.-M. Che, Chem. Commun. 2002, 900.
- 17
- 17aJ.-H. Xie, Q.-L. Zhou, Acc. Chem. Res. 2008, 41, 581;
- 17bY.-M. Li, F.-Y. Kwong, W.-Y. Yu, A. S. C. Chan, Coord. Chem. Rev. 2007, 251, 2119.
- 18
- 18aJ. Y. Lee, O. K. Farha, J. Roberts, K. A. Scheidt, S. B. T. Nguyen, J. T. Hupp, Chem. Soc. Rev. 2009, 38, 1450;
- 18bL. Ma, C. Abney, W. Lin, Chem. Soc. Rev. 2009, 38, 1248.
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